On my 14th birthday, I received a hand-scrawled letter from my grandfather that I have treasured ever since. In it he offered advice on various things: school, work, family, girls – all standard areas to impart wisdom.

But he ended it by saying he looked forward to the day when he could stand on the boundary, watch me approach the wicket with poise and focus, steam in to deliver a ball with pace and swing that knocked the bails clean off as the batsman looked on – still unsure of what shot he should have attempted. Like countless other West Indians of his age, cricket was a way of life, wrapped not only in an almost forensic obsession with the game but of nostalgia for a land left behind. Pride in the West Indian cricket team was prerequisite.

My grandfather sat surveying the field, with one ear plugged into an analogue radio for commentary, while I busied myself tearing confetti from a "four" boundary sign in anticipation of Brian Lara's next big hit. We lost. But it didn't matter – so I was told – because we were a strong team who still gave the English a run for their money.

I wonder what he might think now, as only the rain and an occasional moment of brilliance stands in the way of a weak West Indian side being whitewashed in England. It is the lack of pride in the game among some of the side's top players that makes the prospect of defeat all the more bitter.

The glamour and eye-watering pay cheques of the Indian Premier League has drawn some of the best away from Test cricket and into lucrative contracts which, as cricket historian Hilary Beckles argues, turns the development of West Indian players into "a money-making machine for foreign franchises by producing young talent and mature masters who are released at random with no regard for the goose that lays the golden egg".

Some of the most striking passages in James's autobiography, Beyond a Boundary, recall in vivid detail the race and class hierarchies that plagued the Trinidadian club scene at the beginning of the 20th century, which saw certain clubs off limits for black players. This racism was thrown into stark relief by the ethos of fair play within the game itself, an attitude that many black and brown players had adopted wholeheartedly.

When James, a relatively gifted player, came to choose which club to pick it "plunged me into a social and moral crisis, which had a profound effect on my whole future".

His friend and notably more gifted teammate, Learie Constantine, moved to England to escape the prejudice of the Trinidadian circuit following the 1928 West Indian tour of England. Constantine was appalled at the national side's insistence that a white man should captain the team, an issue he said had "rotted the heart of our cricket".

It would not be until 1960, as the decolonisation process was well under way, that the issue was resolved and Frank Worrell took over the captaincy, and another 20 years until the West Indian team dominated the world stage with their unique brand of bold, fast and sometimes controversial cricket.

Under the captaincy of Clive Lloyd, the West Indian side of the late 70s and 80s reigned supreme. At its centre, Viv Richards, the most brutal test batsman in history, and a fast-bowling quartet – Michael Holding, Andy Roberts, Colin Croft and Joel Garner, dubbed the "four horsemen of the apocalypse", all able to send in a fizzing delivery of over 90mph – who struck fear (and often calls of foul play) into top-order batsman around the world.

Dismantling England in a 5-0 Test series win in 1984, at a time of high unemployment, racism and rioting, players were aware of the significance such a victory had on the British West Indian community: "When the West Indies won," recalled Croft, "people told me they could go to work 'with our backs straight and our heads held high'."

It might feel like misplaced nostalgia to lament the demise of an ideal I was not even alive to fully taste. But as the depleted and aged West Indian crowds attending this year's series might suggest, it may be an ideal that is soon forgotten.